3-氯-5-甲基-2-氧代己酸乙酯 | 111055-64-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 3-氯-5-甲基-2-氧代己酸乙酯
• 英文名称: ethyl 3-chloro-5-methyl-2-oxohexanoate
• CAS: 111055-64-2
• 化学式: C₉H₁₅ClO₃
• 分子量: 206.669
• InChiKey: YFRZNPRSCKZMLY-UHFFFAOYSA-N

物化性质

• 沸点：
  65-67 °C(Press: 3 Torr)
• 密度：
  1.088±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-氯-5-甲基-2-氧代己酸乙酯 在 磷酸二氢铵 、 ammonium hydroxide 、 potassium dihydrogenphosphate 、 葡萄糖 、 magnesium sulfate 、 calcium carbonate 作用下， 以 水 为溶剂， 反应 94.0h， 生成 (2R,3S)-3-Amino-2-hydroxy-5-methylhexanamide
  参考文献：
  名称：

  Highly enantioselective reduction of 3-chloro-2-oxoalkanoates with fermenting bakers' yeast. A new synthesis of optically active 3-chloro-2-hydroxyalkanoates and glycidic esters

  摘要：

  Reduction of 3-chloro-2-oxoalkanoic esters with fermenting bakers' yeast gave optically active 3-chloro-2-hydroxyalkanoic esters 2 (anti(2S,3R)/syn (2S,3S) = 52:48-90:10) in 50-85% yields with >95% ee except for 43% ee of ethy syn-(2S,3S)-3-chloro-2-hydroxy-4 phenylbutanoate (2j). Compounds 2 were treated with NaOEt to give (E)-(2R,3S)-2,3-epoxyalkanoates 3 in 30-66% yields with 44-64% ee. Optically active 2,3-epoxy alcohols (cis-23, trans-23, and trans-25), key intermediates for the syntheses of (-)-disparlure (4), mosquito pheromone (5), and a component of passion fruit flavor (6), were prepared with more than 86% ee in high yields.

  DOI：

  10.1021/jo00054a036
• 作为产物：
  描述：

  Ethyl 2-chloro-3-(2-methylpropyl)oxirane-2-carboxylate 在 aluminum oxide 作用下， 以 xylene 为溶剂， 反应 3.0h， 以68%的产率得到3-氯-5-甲基-2-氧代己酸乙酯
  参考文献：
  名称：

  A Facile Synthesis of 3-Chloro-2-oxoalkanoatesviaThermal Rearrangement of 2-Chloro-2,3-epoxyalkanoates Promoted by Alumina

  摘要：

  描述了一种通过铝土矿促进的2-氯-2,3-环氧烷酸酯的热重排，便捷合成3-氯-2-氧烷酸酯的方法。

  DOI：

  10.1055/s-1987-27923

文献信息

• A Facile Synthesis of 3-Chloro-2-oxoalkanoates<i>via</i>Thermal Rearrangement of 2-Chloro-2,3-epoxyalkanoates Promoted by Alumina
  作者：Sadao Tsuboi、Hiroyuki Furutani、Akira Takeda

  DOI：10.1055/s-1987-27923

  日期：——

  Convenient synthesis of 3-chloro-2-oxoalkanoates via the thermal rearrangement of 2-chloro-2,3-epoxyalkanoates promoted by alumina is described.

  描述了一种通过铝土矿促进的2-氯-2,3-环氧烷酸酯的热重排，便捷合成3-氯-2-氧烷酸酯的方法。
• A Practical Synthesis of Chiral 3-Chloro-2-hydroxyalkanoates and 2,3-Epoxyalcohols
  作者：Sadao Tsuboi、Hiroyuki Furutani、Masanori Utaka、Akira Takeda

  DOI：10.1016/s0040-4039(00)96187-2

  日期：1987.1
• TSUBOI SADAO; FURUTANI HIROYUKI; TAKEDA AKIRA, SYNTHESIS,(1987) N 3, 292-293
  作者：TSUBOI SADAO、 FURUTANI HIROYUKI、 TAKEDA AKIRA

  DOI：——

  日期：——
• Highly enantioselective reduction of 3-chloro-2-oxoalkanoates with fermenting bakers' yeast. A new synthesis of optically active 3-chloro-2-hydroxyalkanoates and glycidic esters
  作者：Sadao Tsuboi、Hiroyuki Furutani、Mohammad Hafeez Ansari、Takashi Sakai、Masanori Utaka、Akira Takeda

  DOI：10.1021/jo00054a036

  日期：1993.1

  Reduction of 3-chloro-2-oxoalkanoic esters with fermenting bakers' yeast gave optically active 3-chloro-2-hydroxyalkanoic esters 2 (anti(2S,3R)/syn (2S,3S) = 52:48-90:10) in 50-85% yields with >95% ee except for 43% ee of ethy syn-(2S,3S)-3-chloro-2-hydroxy-4 phenylbutanoate (2j). Compounds 2 were treated with NaOEt to give (E)-(2R,3S)-2,3-epoxyalkanoates 3 in 30-66% yields with 44-64% ee. Optically active 2,3-epoxy alcohols (cis-23, trans-23, and trans-25), key intermediates for the syntheses of (-)-disparlure (4), mosquito pheromone (5), and a component of passion fruit flavor (6), were prepared with more than 86% ee in high yields.
• Convenient Rearrangement Reaction of 2‐Chloroglycidic Esters by PPh₃: A New Synthetic Method of 3‐Chloro‐2‐keto Esters
  作者：Takuzo Komiyama、Yutaka Takaguchi、Sadao Tsuboi

  DOI：10.1080/00397910600764618

  日期：2006.9

  Abstract A convenient rearrangement reaction of 2‐chloroglycidic esters is reported. Treatment of 2‐chloroglycidic esters with PPh3 under refluxing condition results in the formation of 3‐chloro‐2‐keto esters in good to reasonable yields.

  摘要 报道了一种方便的 2-氯缩水甘油酯重排反应。在回流条件下用 PPh3 处理 2-氯缩水甘油酯导致 3-氯-2-酮酯以良好到合理的产率形成。